5-bromo-1H-pyrrolo[2,3-b]pyridine → 5-Bromo-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 1490470Notes

Reaction equation

HRID 1490470 reaction equation
Brc1cnc2[nH]ccc2c1>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.C[OH2+].C[OH2+].Cc1cnc2c(ccc3c(C)c(C)cnc32)c1C.[Ir].[Ir]>CC1(C)OB(c2c[nH]c3ncc(Br)cc23)OC1(C)C

Participants

6

Reactant 1

HCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 453617795-Bromo-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridineYield 65%

Reagents, catalysts & solvents 4

HCID 742653,4,7,8-Tetramethyl-1,10-phenanthrolineReagentHCID 2733548Bis(pinacolato)diboraneReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Sources & evidence

ORD record
ord-11477037a92942ee8788bfa149551370
Source dataset
Borylation dataset from Roche

Reaction notes

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